While the `shortest` can easily end up being a minor slow road, I would expect the 'fastest' to be biased toward the freeways. But that may vary with the region and length of route.
Usually 'fastest' is based on distance and some sort of estimate of the speed. That speed estimate might a crude one based on road type/name, but might also take into account road surface, grades and curviness. At least with Google Maps in the western states, the differences in speeds between routes seem to be realistic. I can imagine cases in the eastern mountains were short windy route through some pass would end up being both shortest and fastest - at least for a car.
With Google Maps with full internet access it is easy to examine the suggested route for details - terrain mode shows the hills, a zoom in shows the curves, and Streetview shows even more detail. It is also change the route and see how that changes distance and time estimates.
Getting this kind of detail is harder on a phone, or when route finding without internet connection. That's where a degree of preplanning comes in.